A Real Challenge
by Maddygirl4932
Summary: Gary Oak treats women like he treats Pokemon battles; just another thing he has to be the best at. So when new girl, Lane Pewter, enrolls at the Pokemon School of Learning, Gary's already got his sights on conquering her too. But between Lane's avoidance of him and another competitor for her affections, will this challenge be too much? Pokeshipping, Contestshipping, Ikarishipping!


"First day of school and I'm already sick of it," Misty Wallflower, her hair pulled into her signature tomboyish ponytail, announces.

Beside her sit May and Dawn, both of them wearing bags under their eyes like it's some new fashion statement. May tiredly nods her head like a zombie, obviously agreeing with her best friend.

"The first day is always the worst day." Dawn attempts cheerfully, but just ends up flopping her body back on her desk, "-no one can be excited on a day like this."Suddenly there was a boisterous shout that flooded from the hall into their homeroom's open doorway, "MISTY!"

The girls, especially Misty, perked at the noise that was so uncharacteristic for this time of day.

"That has to be..." May said, lazily pushing the pieces in her brain together and raising her head from the desk… "Ash?"

Ash sprinted in like a storm, tripping over chairs and scattering papers as he made his way to the trio. "Misty! I haven't seen you all summer!" He grabbed the redhead in a suffocating embrace, and as she struggled for air, May and Dawn laughed.

"L-let me go, idiot!" Misty shouts, face turning nearly the color of her hair. Her thing for Ash had apparently not faded over the summer.

Ash pulled away pouting, his bottom lip puckered out and his eyebrows drawn together comically, "But Mist, you didn't miss me?"

Misty threw down her fight on top of his head, if only so he couldn't see the blush staining her pale features. "Not at all! I was enjoying the peace and quiet before you got here!"

"Five minutes in and they are already fighting." Dawn smiles, and May laughs.

"Yeah, crazy right? You'd think after a whole summer without seeing each other, they'd be professing their love."

It was then that Drew Hayden, in all his green-haired glory, paused at the door. He glanced inside, locking eyes with May before sighing loudly and calling down the bustling hallway, "Um, excuse me, Miss? I'm afraid that a beast has escaped from the Science Department again." He takes another look at May, his eyes widening dramatically as if seeing her for the first time, "Oh, nevermind. It's just May."

Drew was May's eternal rival/ love. It was obvious they were into each other, but similar to Ash and Misty, were in obvious denial of that apparent fact. He and Gary, yeah Gary Oak, hit it off quite well upon being thrown into this homeroom together three years ago. They were both handsome, charming, and intelligent. They were also both jerks.

"Where is your boyfriend, Hayden?" May shouts back loudly, standing up and pointing a mocking finger at him. Between Ash's shouting and Drew's insult, all her lingering tiredness had evaporated.

"...And they only took a minute to start fighting. New record for May and Drew." Dawn sighed quietly to herself before glancing anxiously at the door for a spotting of purple hair.

"Are you crazy or something?" She jumped at the new voice behind her. Paul!

She swiveled in her chair to look at him- she hadn't seen him in months- and noted he was currently sitting one seat behind and to the right of her own. She counted it as a small victory; he could have sat anywhere else but he had chosen someone close to her.

He looked older, his facial features a bit more defined and hardened in comparison to whom he had been before the summer break. Dawn liked it.

Wait..."C-Crazy?" She asked, finally pulling herself out of her schoolgirlish thoughts to remember what he had even said.

"Tch, you were talking to yourself." Paul explained to her slowly, enunciating each word like she was some sort of idiot. Or Ash.

Dawn blushed and lowered her head. Oh. He had heard that.

"That idiot," Misty mumbled, cracking her knuckles and regaining her spot next Dawn, sitting in front of Paul. Ash settled in the spot in front of her shortly after, completely turning his desk around till he faced her.

"So Misty, Dawn! Did you hear?"

The redhead groaned but Dawn looked at the energetic boy, "What is it Ash?"

"New student! Gary said she's going to be in our homeroom and everything!" Ash says excitedly, nearly bouncing in his seat as he conversated with Dawn.

Her eyes sparkled, "She? As in a girl? Oh my God, do you think she'll have any fashion taste?"

Misty jumped in as well with her own fantasies. "Think she can swim? I need someone who can stand a little water!"

"I wonder if she's a strong Trainer…" Paul added, and just about everyone agreed with that.

"No way! I hope she Coordinates!" May pipes in, stealing back her original seat beside Dawn, "I would love another Coordinator to practice with." She says, glancing at Drew.

The green-haired boy laughs haughtily, "Strange you're asking for another Coordinator to kick your butt. But yeah, I wouldn't mind if I actually had a little challenge in this school."

"I just hope she's a good fuck, you know?" Everyone turns to the door, meeting the familiar face of Gary Oak surrounded by his army of followers. Even after he'd abandoned his entourage of cheerleaders years ago, he still unwillingly carried them around like fruit flies attracted fruit. While he loved the attention and he couldn't help it; his grandfather was the owner of this school, he was rich, hot, and charming- he also didn't want anything to do with most of them beyond a superficial hook-up. He was everything a girl ever wanted, except he wanted none of them.

"Oh, no, no, no, no, no!" Misty says, jumping up like a hellstorm and wagging her pointer finger in his face, "You will NOT touch my new swimming buddy!"

Gary effortlessly laced his fingers around her small wrist and craned his neck so they were only inches apart. "Then can I touch you?"

His whole fanclub gasped before departing into their seats- they knew when to back off. Like trained puppies, they turned tail and left whenever things were getting intimate, per his request. Gary, however, knew it would never get 'intimate' between Misty and himself. She was Ashy-boy's girl, and while he was a dick in every sense of the word, he was also a loyal friend.

Speaking of Ashy-boy, he was fuming, and Gary smiled. Loyal or not; it didn't mean he couldn't get his best friend riled up.

Misty barely blinked. "You must have a deathwish, Oak. I'll give you to the count of three. One-" She didn't even get to two. Gary, and everyone else in the class, knew better than to mess will the spunky redhead.

He released her wrist, "Then I make no promises about your 'swimming buddy.'"

Gary fell into the closest seat, beside Drew who had conveniently sat in front of May. "Your hair is still green." He noted casually.

"Yeah?" Drew said, narrowing his eyes at his spiky-headed 'companion', "-And it's going to remain this color… you know, for forever."

"Oh, I guess I'm just surprised it hasn't turned pink or something." Gary responded, picking at his nails and smirking from the corner of his eye at Drew.

"What is that supposed to mean?!" Drew shouted, causing Gary to chuckle.

"You haven't asked May out yet, grass-head." He whispered, careful so that May didn't hear, "That makes you a pansy-ass, like a flower. You head should be pink, not green, for being a wimp."

Drew swatted at Gary before crossed his arms and looking away to hide the flushing of his cheeks, "Shuddup. I don't like May. She's a brat."

Ash leaned over and poked Drew's pink face face, "Oh Drew, you better do it soon! You're hair's going to turn pansy-colored too."

"Like you're much better!" Drew shot back at Ash.

Ash shrunk in his seat and glanced at Misty, who was engaged in an animated conversation with Dawn and May about the new girl. She was beautiful, and even if they were the best of friends, she seemed untouchable. She was so smart, and pretty, and caring (when she wanted to be)...and he was...Ash...

It had been nearly six years since he'd met her by the river- she'd been fishing and he, well, he had been drowning. Her hook had caught him, and his heart that day, as he was reeled in like a Magikarp and then proceeded to flop on land awkwardly like one for a few minutes. Thinking back, he should have pretended to be unconscious. At least then, Misty would have given him CPR. As a Waterflower, she was trained in that stuff, you know.

Anyhow, they hung out all summer and found themselves in the same homeroom- this homeroom- a few years ago. He'd thought about her ever since that day, and each year, promised himself he'd finally ask her out. That never happened, of course.

"Misty, I-" Ash hardened his resolve; he would do it. This would be the year, no doubt!

"Hello, students!" Their homeroom teacher, Cynthia stood in front of the classroom, a girl tucked quietly under her arm.

Ash looked past Drew to look at Gary, who was watching his next pursuit with a calculated expression. Ever since he'd given up the trainer life for Pokemon research, Ash had realized his best friend had begun treating girls like matches. He had to win and predict everything.

Gary began with her looks; the girl was naturally tan, a light brown that was lighter than Iris' skin tone but much darker than Ashy-boy's. Her hair was spiky and messily piled to the side, nearly covering an eye and it looked very tomboyish- not his style, as he preferred his girls to have long hair, but short admittedly suit her better.

The new girl's exotic charm didn't end there, however. She had plump, awkward lips that were just dying to be bitten between his teeth and large, almond shaped eyes. Her body was hidden beneath and oversized sweatshirt, but he could see the inkling of hips and good-sized butt underneath it.

He could tell the new girl wasn't as skinny as May or the traditional beauty Dawn was with her long blue locks and short dresses that left little to the imagination. But that didn't matter; Gary had a very 'good' imagination. A sweatshirt and some jeans wouldn't deter him from wanting to unwrap that chocolate bar.

Her appearance, overall, was rough and down-to-earth, which he liked. The closest thing he got to that was Misty, but she was off limits due to the bro-code.

Gary continued to observe the new girl; classifying her, taking mental notes about her, and reading her like he would any Pokemon. He could see the illusion she was trying so hard to maintain- she was like a Misdreavus using psychic- as in her appearance said one thing while her body language was telling a completely different story.

Firstly, the new girl was shifting her weight; back and forth, back and forth, like an MMA fighter preparing to fight. She wasn't dangerously doing it- she was nervous and probably ready to run. She was also covering her chests protectively with her arms, while her fingertips which peaked out from underneath her armpits, were shaking violently. Even her voice, as she introduced herself as Lane, shook beyond her control.

The new girl was like a bunny in a bulldog costume.

Gary leaned over in his seat to whisper in Drew's ear, "Drew, how long do you give me to get into her pants?"

He watched as Drew shook his head disapprovingly at his lifestyle before looking the girl critically up and down. After a moment, Drew turned back to whisper in his ear, "Week, tops. She doesn't look that hard."

Gary frowned, disgusted at his friend's poor judgement. No, that was too easy. This girl is a virgin- he could practically smell it on her. And virgins always took the longest; spewing crap about 'waiting for the right one' and 'marriage' when a month later, they're lying face down in his sheets, asking when they would meet up next time. There never was a next time.

"A month. I can do it in a month." He said confidently, following the girl with his eyes as she took the furthest seat in the classroom. Next to Paul, of all people, who promptly ignored her. She didn't seem to mind, instead focusing all her energy on Cynthia, who was going through all the first day procedures, and calming her twitching hands.

Oh yeah, this would be a fun month.

0o0oo0o0o00o0o0o0ooo0o0o0o0o0o0o0o0o0o0o0o0o0o0o0

"It's a shame she doesn't have fashion sense," Dawn cried dramatically into her arm, "But she seems nice enough. I vote to adopt her into the group."

Drew strolled up beside the trio of girls and Ash, walking backwards in front of May, "I wouldn't do that. Gary's got his sights on her and we all know what happens after that..."

"Hook-line-and-sinker," May sighed unhappily, "If she gives into Gary, she'll just become another mindless drone."

"I can't let that happen!" Misty shouted, gaining a few looks from a group of students they were passing, "She hasn't even decided on a profession! I-I can convert her to Pokemon Tranerism!"

Ash ran a hand through his unmanageable black hair and sighed, placing his other hand on her shoulder, "Mist, you know how Gary is. There is nothing that'll stop him from getting the girl."

Misty grimaced. As much as she liked Gary, which she kind of had to, as he was Ash's best friend, he really was an inconsiderate jerk. All she wanted was another girl who wouldn't become a mindless slave of Gary's, that's all. The only ones who were untouchable were May, Dawn, and herself, and only because preying on them was picking a fight with Drew, Paul, and Ash.

Could she use that to her advantage?

"I wouldn't bother, Misty." Dawn says sadly. She was really taking this hard. With Gary on the prowl, she truly believed there was no hope. "When I first came to this school, I almost fell for Gary's charm as well. Then I realized what a jerk he was…"

May could tell Dawn was mentally kicking herself again. Out of all of them, she had the hardest time adjusting to Gary's constant flirtings and sex buddies. When she had first arrived at the school, for her obvious good looks and bubbly personality, she had been targeted by Gary. After truly falling for him, she had the unfortunate pleasure of overhearing that she meant little-to-nothing to him. She 'dumped' him and he arrived the next day with a black eye- May was positive Paul, who had never appreciated Gary's musings, had given it to him- while Dawn, after three years, still felt awkward and upset with herself around him.

May cupped an arm around her blue-haired friend's shoulders. "Shut up, Dawn," she commanded, "We are sick of this too. Because of Gary's shenanigans, all the girls obsessively stalk our group while all the boys hate our group."

"I've got an idea, Dawn." Misty said, smiled broadly, "Gary doesn't mess with taken girls. Or us."

Ash snapped his fingers together, "Yeah, Gary always talks about some code he follows."

Drew flipped his hair out of his eyes. "Bro-code," he clarified.

"Yup, that's it." Ash nodded, smiling at Misty as if he had discovered the meaning of life.

She stopped everyone in their tracks and rounded on them with fierce cerulean eyes, a look Ash loved, and pumped a clenched fist in the air with vigor, "We won't let Gary have our possibly fashion-sensed-water-loving-trainer-coordinator!"

Everyone but Drew cheered, but as he watched May pump her own fist in the air, he couldn't help but smile.

He knew this extended past wanting a new addition to their group. It was about winning against Gary, who always seemed to get whatever he wanted. There was a lot more at stake then some silly, forgettable girl's heart- it was a Civil War threatening to break out between his posse and he knew that no matter the turn out, it would be something spectacular.

0o0oo0o0o00o0o0o0ooo0o0o0o0o0o0o0o0o0o0o0o0o0o0o0

Lane busied herself with her shoes, watching them as she speedwalked like they were the most interesting things around. Anything to avoid the curious stares, and glares, of the student body. She had never liked attention- despised it, really- so to be stared at, and with such venom, she was nearly shaking in her converses. But that wasn't what truly unnerved her…

She glanced back, catching sight once again of the tall, spiky-haired brunette in her peripheral vision. He'd been following her for at least of few minutes, and the bell for next period would ring in less than a minute. She was lost, but… what was he?

Her hand clenched around the device in her hand. It was small and red with a metal ring sticking out from the top, waiting to be pulled. She wrapped her finger around the ring.

Someone's hand fell on her shoulder. "Hey."

It was the boy, Gary, if everyone's whispers were correct. I recognized him immediately. H-He had been staring at me earlier. "Lane… you're in my homeroom."

"Glad you remember, sweetie. Where are you headed?" He asked, leaning in close enough that Lane could smell the mint leaves on his breath. Freshly brushed and obviously expecting something- this guy was trouble. She stepped back, creating some distance between them, finger still looped around the device.

Biology. "Chorus." Lane lied. She wouldn't dream of letting this creep get comfy with her schedule, you know, like the serial killers do in the Lifetime movies. "Speaking of which, the bell is going to ring. I-I need to go."

She turned to leave but his fingers laced around her wrist, pulling off the pin and swinging her back until she was plush against his chest- it was just like a romantic movie. Well, except for the fact that she hardly knew this guy's last name and… he had made her set off the device.

All of a sudden, a loud beeping noise flooded her eardrums and filled the air, coming from the red little device in her hands. She tore herself away from Gary, which wasn't hard as he was pretty shocked himself, and looked from the device to his face, back to the device. The few remaining students in the courtyard turned to glare at the cause of the offending sound, and Lane felt as if she were going to melt from the pressure. She began to shake uncontrollably and fought back tears.

"What is that!" Gary shouted over the loud beeping noise. He looked irritated, brows drawn together sharply, lips down turned, and hands pressed to his ears to help block some of the deafening noise.

"A r-rape alarm!" She called back, cupping her mouth while her brown cheeks flushed. She couldn't believe her luck; this was so embarrassing. If things had gotten out of hand, she would have showed him as a warning but… she had never planned on using it!

Lane dropped to her knees and began moving her hands around blindly on the ground. It was a thin, metal pin that had to be reinserted into the red device in order to silence it. She had accidently pulled it when Gary had pulled her into his chest. Why had he done that?

"C'mon!" Gary shouted over the noise, reaching down to pull her back off the ground. "We can't stay here. We've got to move unless you want to get in trouble on your first day!" She didn't hesitate and dropped the incriminating alarm; there was no way she would end up in the principal's office! First day or not, she was not a trouble maker! And just like that, she was being pulled by Gary Oak, through the crowd, through the high school, and finally to Biology class.

They were late, sweaty and huffing when they arrived, knocking painfully at the closed door of the classroom. "Can't say that wasn't fun…" Gary said, smirking, and she wasn't sure if he was joking or not.

"Y-Yeah. Sure." Lane replied gruffly, just as the teacher came and unlocked the door. She looked up into the familiar face and gasped, "N-No way. This has to be a mistake!"

Gary looked from her to the teacher, confusing settling into his features, "Brock! You work here?"

Brock frowned, Lane frowned, and Gary frowned before saying in unison, "Wait. You know each other?!"


End file.
